Dimethylformamide → 3,5-Diethoxybenzaldehyde

HRID 1094050Notes

Reaction equation

HRID 1094050 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].Br[CH2:12][CH3:13].[C:14]([O-:17])([O-])=O.[K+].[K+].[CH3:20]N(C=O)C>>[CH2:12]([O:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([O:17][CH2:14][CH3:20])[CH:9]=1)[CH:5]=[O:6])[CH3:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 943653,5-Dihydroxybenzaldehyde

Product 1

HCID 226086163,5-Diethoxybenzaldehyde

Conditions

Temperature
60 °C

Procedure

An amount of 3,5-dihydroxybenzaldehyde (56a, 500 mg, 3.62 mmol) was dissolved in 10 mL DMF, anhydrous. It was added (2.0 g, 18.1 mmol) of bromoethane and 733 mg (5.34 mmol) of K2CO3. The reaction mixture was heated to 60° C. for 4-5 hrs. Afterwards, 100 mL of EtoAce was added to the reaction mixture, and the reaction mixture was washed with brine (3×200 mL). The organic layer was dried over Na2SO4 and evaporated in vacuuo to afford 3,5-diethoxybenzaldehyde (56b) which was carried onto the next step without further purification. MS [m+H] calc'd for C11H14O3, 195.10; found 195.10.

Workup

  1. additionAfterwards, 100 mL of EtoAce was added to the reaction mixture
  2. washthe reaction mixture was washed with brine (3×200 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated in vacuuo

Sources & evidence

ORD record
ord-c36e027e3cce485caf4df0afc02463fe
Source dataset
uspto-grants-2012_03
Patent number
US08133898B2

Reaction notes

Loading…